Location: Winter Haven
Do Not Show Listings
240 SANTA ROSA DR, WINTER HAVEN, FL 33884
$439,000178 Days on yellowkey MLS ID: L4958092
1 Days Off yellowkey (back on 5/29/2026)
INCREASED by $4,100 (0.9%) on 05/17/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2850 Built: 1988Monthly Fee: $46 Tax: $2,790 (2023)Community: Overlook Ests Ph 3Spa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,790
Elementary School: Elbert Elem
High School: Winter Haven Senior
Tax Year: 2023
Middle School: Denison Middle
Remarks: Beautiful 4 bedroom, 2 1/2-bathroom, pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the rare opportunity you've been waiting for: a spacious, ultra-private luxury home in a top-tier location. Schedule your showing today and make this dream residence yours before it's gone.
Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)
Listing Agent: Brian Surrency (863-204-4298)
1220 33RD ST NW, WINTER HAVEN, FL 33881
$139,98725 Days on yellowkey MLS ID: A4694880
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1141 Built: 1926 Tax: $2,340 (2025)Community: West Cannon HeightsSingle Family
Taxes:$2,340
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Charming 3-bedroom, 1-bath home with no HOA, offering a great opportunity for investors or first-time buyers alike. Conveniently located in Winter Haven with easy access to shopping, dining, schools, major roadways, and everyday amenities. This property offers plenty of potential and is ideal for those looking to expand their portfolio or create a place to call home.
Listing is courtesy of: JOSEPH WALTER REALTY LLC (248-294-7850)
Listing Agent: Scott Fader (248-294-7850)
247 S LAKE PANSY DR, WINTER HAVEN, FL 33881
$469,90068 Days on yellowkey MLS ID: TB8496517
REDUCED by $10,000 (2.1%) on 05/10/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2247 Built: 1986Monthly Fee: $136 Tax: $2,948 (2025)Community: Hartridge HillsSingle Family
Taxes:$2,948
Remarks: OWNER FINANCING AVAILABLE ~ LAKEFRONT 3 BEDROOM / 2 BATH HOME WITH PICTURESQUE OPEN WATER VIEWS AND PRIVATE 30 FT DOCK! Located directly on Lake Pansy in the gated subdivision of Hartridge Hills, a quaint lakefront community of approximately 60 homes. NEWER ROOF 2022 and NEWER GENERAC GENERATOR 2020. Lot size is 150 X 83 ft directly on Lake Pansy. Additional lot size in records of 2.44 acres includes riparian or water rights into the lake. Beautiful stone working fireplace with vaulted ceiling in the great room. Spacious kitchen with plenty of storage and breakfast area overlooking tranquil water views. Home was originally constructed with 2,247 sq ft and later the expansive back porch was enclosed bringing the total to 2,958 sq ft of air-conditioned living space under roof. Large windows and sliding glass doors frame panoramic vistas, infusing the space with a sense of tranquility and connection to nature. Attached 2-car garage with large storage room. HOA fees include lawn care, trimming and fertilizer to give you more time to relax. Access to Lake Hartridge and the ‘Chain of Lakes’, a navigable canal system connecting 15 lakes, is obtained from the private community boat ramp and dock. This community is well known and desired by aircraft owners and flying enthusiasts as it is near Gilbert Field-Winter Haven Regional Airport, a city-owned airport that supports over 80,000 flights a year. It is also home to the Jack Brown Seaplane Base renowned as the largest and one of the oldest seaplane training and base operations in the world. Conveniently located between Orlando and Tampa with great attractions, waterfront restaurants, shopping, and some of the best fishing and ski lakes available! Welcome home to endless days of sunshine and relaxation. Please see the interactive 3D virtual tour and floor plan. Virtually staged photos are included.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Kay Szinegh (813-918-0624)
239 SUNFISH DR, WINTER HAVEN, FL 33881
$315,00051 Days on yellowkey MLS ID: O6403244
3 Days Off yellowkey (back on 6/2/2026)
REDUCED by $10,000 (3.1%) on 05/13/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1996 Built: 2021Monthly Fee: $92 Tax: $5,146 (2025)Community: Lake LucurneSingle Family
Taxes:$5,146
Elementary School: Lake Alfred Elem
High School: Haines City Senior High
Middle School: Boone Middle
Remarks: Welcome to 239 Sunfish Dr, a 4-bedroom, 2-bath home in one of Winter Haven’s growing communities, offering modern comfort, thoughtful upgrades, and outdoor spaces designed to be enjoyed year-round. Built in 2021 and offering nearly 2,000 square feet of living space, this home is move-in ready and packed with value for homeowners and investors alike. Inside, you’ll find a spacious open-concept layout with a split-bedroom floor plan that offers both functionality and privacy. The kitchen opens seamlessly to the main living and dining areas, creating the perfect flow for everyday living and entertaining. With four full bedrooms, there is plenty of space for a growing household, guests, or a home office setup. What truly sets this home apart is the outdoor living experience. Enjoy a fully screened-in back porch, perfect for relaxing in the evenings without worrying about bugs, plus an extended outdoor living area ideal for grilling, gathering, or simply unwinding. A custom paver walkway leads to a charming gazebo, creating the perfect shaded retreat to enjoy the outdoors while staying out of the Florida sun. Whether you're hosting friends or enjoying a quiet morning coffee, this backyard was designed to be used and enjoyed. Additional upgrades include a full gutter system for added function and protection, helping direct water away from the home and adding peace of mind during Florida’s rainy season. Located in a growing area of Winter Haven with convenient access to shopping, dining, schools, and major roadways, 239 Sunfish Dr offers the perfect blend of newer construction, smart upgrades, and comfortable Florida living. Whether you're looking for your next home or a strong long-term investment, this one is easy to love.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Noah Stevens (863-400-1172)
35 S LAKE FOX RD, WINTER HAVEN, FL 33884
$399,999304 Days on yellowkey MLS ID: O6337767
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2149 Built: 1981 Tax: $2,600 (2023)Community: N/ASpa: NoSingle Family
Taxes:$2,600
Remarks: Lakefront living on nearly 2 acres! This 3 bedroom, 3 bath home sits on 1.74 acres along the private shores of Lake Fox. Offering over 2,100 sq ft of living space, the property features spacious common areas, vaulted ceilings, and large windows with serene lake views. The split floor plan includes a generous primary suite, two additional bedrooms, and multiple living and dining spaces. The property is perfect use for a mother-in-law suite with two separate enclosed patios. Outside, enjoy mature trees, a peaceful setting, and direct access to the water. With a newer roof (under 3 years old) and no HOA restrictions, this property provides the perfect opportunity to update or customize to your vision. Conveniently located near shopping, dining, and major roadways, this lakefront home offers privacy and potential in the heart of Winter Haven. MOTIVATED SELLER!
Listing Agent: Michele Rueff (321-948-4332)
3744 GIORGIO DR, WINTER HAVEN, FL 33884
$274,900144 Days on yellowkey MLS ID: O6377486
2 Days Off yellowkey (back on 6/2/2026)
REDUCED by $9,690 (3.4%) on 05/29/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1665 Built: 2025Monthly Fee: $17 Tax: $6,636 (2025)Community: Villamar Phase 6Single Family
Taxes:$6,636
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Middle School: McLaughlin Academy Of Excellence
Remarks: Under Construction. Introducing the Harper floorplan at Villamar, where every square foot is put to use with sophistication and comfort. Inside this 4 bedroom, 2 bathroom home, you’ll find 1,665 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing granite and tile floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The chef's kitchen is a true highlight, boasting granite countertops, sleek stainless steel appliances, and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. The four generously sized bedrooms offer flexibility for various lifestyles. The primary suite is a tranquil retreat, featuring a private ensuite bathroom with dual sinks, a separate shower, and a walk-in closet. The remaining three bedrooms share one well-appointed bathroom, making morning routines a breeze. Like all homes in Villamar, the Harper includes all concrete block and also smart home technology, which allows you to control your home anytime with your smart device while near or away. Whether you're seeking a peaceful family retreat or a stylish place to call your own, this home is sure to meet your every need. Contact us today and find your home at Villamar. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Paul King (407-519-3940)
333 MEREDITH BLVD, WINTER HAVEN, FL 33881
$356,94025 Days on yellowkey MLS ID: O6410465
4 Days Off yellowkey (back on 6/2/2026)
INCREASED by $15,000 (4.4%) on 05/26/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2371 Built: 2026Monthly Fee: $6 Tax: $2,808 (2025)Community: Willowbrook NorthSingle Family
Taxes:$2,808
Elementary School: Fred G. Garnier Elem
Remarks: Under Construction. The Ponte Vedra floor plan at Willowbrook North offers spacious two-story living with 5 bedrooms, 3 full baths, and approximately 2,371 square feet of thoughtfully designed space. This open-concept home features a modern kitchen overlooking the great room and dining area, a spacious primary suite, flexible living areas, and available options. Located near Lake Fannie and adjacent to Willowbrook Golf Club, Willowbrook North offers scenic surroundings with convenient access to shopping, dining, parks, downtown Winter Haven, and major commuter routes to Orlando and Tampa. Buyers will also enjoy energy-efficient features and modern interior finishes.
Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)
Listing Agent: Adam Schott (407-270-2747)
148 LAKE OTIS RD, WINTER HAVEN, FL 33884
$459,000152 Days on yellowkey MLS ID: L4958667
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2663 Built: 1974Monthly Fee: $100 Tax: $6,141 (2025)Community: LakewoodSingle Family
Taxes:$6,141
Remarks: Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level home offers a perfect blend of modern luxury and comfort. With a spacious layout, a private pool, and an abundance of natural light, this home is designed for both relaxation and entertaining. As you enter, you’ll immediately notice the bright and airy atmosphere created by large windows that allow natural light to flood the home. The home features stunning luxury vinyl plank flooring and a beautiful brick fireplace, adding warmth and character to the space. The kitchen is of good size and boasting sleek countertops, new modern appliances, and ample cabinet space. Enjoy casual meals in the eat-in kitchen or step outside to the screened-in porch, an ideal spot for dining al fresco or simply relaxing while overlooking the expansive backyard and pool. Come add your personal touches and make this house your beautiful home!
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Michelle Armbruster (863-521-6879)
221 AVENUE F SE, WINTER HAVEN, FL 33880
$185,00072 Days on yellowkey MLS ID: L4960995
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 804 Built: 1948 Tax: $1,272 (2025)Community: Berry J B SubSingle Family
Taxes:$1,272
Remarks: Back on market! Cute as a button, historic charm with some nice updates. From the welcoming front porch to the massive fenced back yard, complete with dog washing station, this is a cozy spot to call home! Love the original hardwood floors, open bright kitchen, and character such as built ins. Roof is less than 10 years old, and the sellers have updated the HVAC including adding a mini split to the main bedroom for those who like it extra cold at night. Plenty of parking and extra storage outside as well...check this one before it gets away!
Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)
Listing Agent: Paula Shields (863-581-1498)
120 4TH WAHNETA ST E, WINTER HAVEN, FL 33880
$150,00095 Days on yellowkey MLS ID: B4902213
0 Days Off yellowkey (back on 3/25/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 864 Built: 1956 Tax: $809 (2025)Community: Wahneta FarmsSingle Family
Taxes:$809
Remarks: Under contract-accepting backup offers. Step inside through the large enclosed foyer—perfect as a welcoming entryway, mudroom, or additional sitting space. The home features a comfortable living room and a well-appointed kitchen with a separate dining area, ideal for everyday living and entertaining. A bonus back room provides flexibility and can easily be used as a home office, hobby room, or additional living space. Enjoy outdoor living on the covered back porch overlooking a fully fenced yard—perfect for pets, gatherings, or simply relaxing in your own private oasis. The property is a true gem for those who love fresh fruit, featuring numerous mature trees including mango, avocado, peach, lemon, and other citrus varieties. Additional highlights include two large storage sheds with electricity already in place, offering excellent space for a workshop, storage, or creative projects. There is also a full RV hookup with electric, water, and septic—perfect for travelers or accommodating guests. This property offers a rare combination of comfort, utility, and outdoor enjoyment. Don’t miss this opportunity to own a home with so much to offer!
Listing is courtesy of: LAND SOUTH REALTY, LLC (863-937-8867)
Listing Agent: Ron Denney (863-660-3919)
1645 AVENUE C NE, WINTER HAVEN, FL 33881
$229,999120 Days on yellowkey MLS ID: A4683425
0 Days Off yellowkey (back on 6/2/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1204 Built: 1959 Tax: $3,012 (2025)Community: Lake Elbert Heights Unit 02 02 RepSingle Family
Taxes:$3,012
Remarks: Back on market buyers financing fell through. Welcome home! Your forever home is located near downtown Winter Haven and just a short distance from Polk State College. Completely remodeled in 2021 with a New Roof, New A/C, New Water Heater, New Electrical system, new windows new kitchen (Quartz Countertops), new appliances, new floors (Vinyl). This home has a huge, oversized corner lot and with summer around the corner, this will be the place for all the summer BBQ's.
Listing is courtesy of: FLATFEE.COM (954-965-3990)
Listing Agent: Cliff Glansen
352 VAIL DR, WINTER HAVEN, FL 33884
$274,90019 Days on yellowkey MLS ID: L4962337
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2040 Built: 1990Monthly Fee: $17 Tax: $1,538 (2025)Community: Cedar Cove Ph 02Single Family
Taxes:$1,538
Remarks: Move-in ready and priced to sell! Located in a quiet, neighborhood with a low HOA of just $200 annually, this beautifully updated 3-bedroom, 2-bath home offers exceptional value, major system updates, and endless potential on a spacious quarter-acre lot. Step inside to discover an inviting open-concept layout where the living room, dining area, and kitchen flow seamlessly together, creating the perfect space for both everyday living and entertaining. The updated kitchen features modern cabinetry, updated fixtures, appliances, and a center island that serves as the heart of the home. Luxury vinyl plank flooring throughout provides a clean, cohesive look and easy maintenance. Designed with privacy in mind, the split-bedroom floor plan offers a spacious primary suite separated from the guest bedrooms. Every bedroom features a walk-in closet, providing ample storage throughout the home. A large Florida room adds valuable additional living space and connects the home’s interior, making it ideal for a home office, playroom, gym, media room, or second living area. Outdoor living is where this property truly shines. Situated on approximately a quarter-acre lot, the expansive backyard offers plenty of room to create your dream outdoor oasis, including space for a future pool. Enjoy peaceful views with acreage behind the property, providing added privacy and a more open feel than many neighboring homes. The 16x16 screened patio with a concrete slab is perfect for relaxing, entertaining guests, or enjoying Florida evenings year-round. Major updates provide peace of mind, including a 2021 roof and 2021 A/C system. Originally constructed with a tile roof design, the home was built to support the additional structural load, contributing to its durability and long-term appeal. Additional highlights include a two-car garage, vinyl privacy fencing, updated appliances, modern fixtures, and thoughtful improvements throughout. Offering a rare combination of location, lot size, recent updates, low HOA fees, and future potential, this property presents an outstanding opportunity in one of the area’s most desirable neighborhoods. Whether you’re looking for a move-in-ready home, additional space to grow, or a property with room to personalize over time, this home checks all the boxes. Seller is motivated. Schedule your private showing today and discover everything this exceptional property has in store.
Listing Agent: Emily Ward (863-632-1865)
3305 ROYAL TERN DR, WINTER HAVEN, FL 33881
$240,000114 Days on yellowkey MLS ID: O6385959
3 Days Off yellowkey (back on 5/18/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1725 Built: 2021Monthly Fee: $10 Tax: $6,004 (2025)Community: Lakeside Lndgs Ph 3Single Family
Taxes:$6,004
Remarks: Under contract-accepting backup offers. Short Sale. ***SHORT SALE*Discover Your Dream Home at Lakeside Landing! Welcome to this immaculate home in the picturesque community of Lakeside Landing! This property offers the ultimate in modern living, combining comfort, style, and functionality. It's move-in ready and equipped with smart home technology, energy-efficient windows, and SOLAR PANELS to help you save on energy costs. Plus, enjoy the privacy of having no rear neighbors and a fully fenced large yard. Recent Upgrades and Features Flooring: Experience the elegance of luxury vinyl flooring throughout the home, with upgraded plush carpeting in the primary bedroom. The bathrooms boast stylish tile flooring. Bathroom Updates: Enjoy the convenience of brand-new toilets and an updated guest bathroom that features a new vanity and mirror. Kitchen Enhancements :Crown molding on kitchen cabinets Added cabinet hardware, Stunning new backsplash, Farm-style door leading to the pantry New wooden pantry shelves Additional Interior Features: Ceiling fans in both the primary bedroom and living area Neutral color scheme with fresh, whole-house interior paint Outdoor Living Relax and unwind on your screened-in porch while overlooking your spacious, fenced yard. It's the perfect spot for enjoying a morning coffee or evening gatherings with friends and family. Community Amenities Lakeside Landing offers a variety of community features to enhance your lifestyle, including: Resort-style pool: Dive into relaxation and enjoy the sun by the pool. Ideal Location Convenience is at your doorstep with easy access to major highways like 27 and I-4. Nearby attractions include Legoland, Disney World, and Universal Studios, making this home an ideal location for entertainment enthusiasts. Additionally, Posner Park is just around the corner for all your shopping needs. Don't miss the opportunity to make this like-new, energy-efficient home yours. Come check it out and experience the best of Lakeside Landing living!*CDD INCLUDED IN TAXES . OWNER MOTIVATED
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Brenda Anglada (407-493-3464)
4 CASARENA CT, WINTER HAVEN, FL 33881
$524,00074 Days on yellowkey MLS ID: P4938356
REDUCED by $5,000 (0.9%) on 05/29/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3911 Built: 1984Monthly Fee: $320 Tax: $4,267 (2025)Community: Casarena On The LakesSingle Family
Taxes:$4,267
Remarks: This dynamically unique home in Winter Haven offers waterfront living, with direct access to the renowned Chain of Lakes. Ideally situated on Lake Cannon, the property delivers stunning water views and a peaceful setting that’s hard to match. Located within a gated, low-maintenance community, this home allows you to enjoy all the perks of ownership without the added upkeep. The community pool and hot tub sits just steps away—offering the feel of a personal pool without the responsibility. Residents also enjoy access to a community dock with first-come, first-served boat slips, making it easy to embrace the lake lifestyle. The property itself features a fenced yard, and a beautiful pergola—perfect for relaxing, entertaining, or enjoying the serene lakefront setting. The garage is equipped with a 2021 split-unit AC system, creating a versatile space ideal for a workshop, gym, or even additional living area. For added peace of mind, the home includes a gas-powered generator that automatically kicks on when needed. Inside, the home is nothing short of impressive—boasting soaring cathedral ceilings, expansive balconies with breathtaking views, and a layout that is both majestic and thoughtfully designed. The primary suite is a true retreat, featuring a private balcony, dual vanities, and a luxurious soaking tub designed for relaxation. Additional office and bonus spaces offers flexibility and can easily be converted into extra bedrooms to fit your needs. Updates include two AC units installed in 2017, along with a durable metal roof added in 2021 and the roof tiles were sealed and coated for an extra long life. Whether you’re looking for a full-time residence, a seasonal getaway, or a place to gather with family and friends, this home delivers a warm, inviting atmosphere with unique architectural character throughout. Enjoy peaceful mornings overlooking the lake, afternoons gardening in your yard, or evenings unwinding on the balcony while taking in the surrounding wildlife. Conveniently located near shopping, grocery stores, and Home Depot, this is more than just a home—it’s a lifestyle. A property like this must be seen in person to truly appreciate the grandeur and exceptional living experience it offers.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Keith St. Onge (863-651-1397)
2117 HIGH POINT AVE SW, WINTER HAVEN, FL 33880
$389,90047 Days on yellowkey MLS ID: L4960940
2 Days Off yellowkey (back on 6/1/2026)
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2485 Built: 1977 Tax: $6,491 (2025)Community: High PointSingle Family
Taxes:$6,491
Elementary School: Lake Shipp Elem
Remarks: This spacious 4-bedroom, 3-bathroom home offers the perfect blend of comfort and functionality. Featuring a large living room, there is plenty of space for relaxing, entertaining guests, or enjoying time with family. The open and inviting layout flows beautifully throughout the home, creating a warm and welcoming atmosphere.Step outside to your own private pool, perfect for enjoying Florida’s sunshine year-round, hosting weekend gatherings, or simply unwinding after a long day. With generous bedroom sizes and three full bathrooms, this home is ideal for families or anyone looking for extra space and convenience.Located in a desirable Winter Haven area, this property combines spacious indoor living with fantastic outdoor amenities, making it a wonderful place to call home.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Marissa Hipp (863-624-4995)
5041 KAIA AVE, WINTER HAVEN, FL 33884
$260,00039 Days on yellowkey MLS ID: TB8502452
REDUCED by $32,870 (11.2%) on 06/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1269 Built: 2026Monthly Fee: $15 Tax: $5,000 (2025)Community: VillamarSpa: NoSingle Family
Taxes:$5,000
Remarks: Under Construction. Brand new, energy-efficient home available by Jun 2026! Prepare dinner while catching up on the day’s events from this home's chef-inspired kitchen which overlooks a great room. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.
Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)
Listing Agent: Bryan Sumner (813-336-5895)
440 KENSINGTON VIEW DR, WINTER HAVEN, FL 33880
$263,000188 Days on yellowkey MLS ID: G5105497
1 Days Off yellowkey (back on 4/15/2026)
INCREASED by $23,000 (9.6%) on 04/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1688 Built: 2020Monthly Fee: $53 Tax: $3,809 (2024)Community: Kensington ViewSingle Family
Taxes:$3,809
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Short Sale. BANK APPROVED AT 263K --VACANT---ON A CORNER LOT--delightful home boasting a private vinyl fenced side and backyard. Step inside to find three bedrooms and two bathrooms, where the primary suite offers serene privacy and comfort. The kitchen is a homeowner’s dream with upgraded granite countertops, complemented by stylish brown cabinets. Hard flooring flows throughout most of the home, providing both beauty and durability, while the cozy carpet in one guest bedroom offers a touch of warmth. Freshly painted walls and even the ceiling fan in the family room have just been updated, giving the whole space a fresh, inviting feel. Additionally, a covered lanai provides a perfect spot for relaxation or entertaining. Easy access to the Polk Parkway to Orlando And Tampa,
Listing is courtesy of: PREFERRED RE BROKERS III (407-440-4900)
Listing Agent: Michael Huculak (321-624-0150)
4020 CARTERET DR, WINTER HAVEN, FL 33884
$405,900102 Days on yellowkey MLS ID: O6389154
REDUCED by $14,000 (3.3%) on 05/22/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2282 Built: 2015Monthly Fee: $484 Tax: $3,537 (2025)Community: TraditionsSingle Family
Taxes:$3,537
Remarks: NEW PRICE ADJUSTMENT-Seller is willing to offer 3K towards Buyer's Closing Costs. Welcome to 4020 Carteret Dr in Winter Haven, a beautifully updated 4-bedroom, 3-bath home located in a desirable 55+ lakefront community with a 3-car garage offering comfort, convenience, and low-maintenance living in the heart of Central Florida. This thoughtfully designed home features stunning lake views, hardwood flooring, an updated kitchen with modern finishes, and stylish upgrades throughout. The spacious layout includes a mother-in-law suite, perfect for visiting family, guests, or additional privacy. Residents enjoy direct water access and a private community boat ramp, providing easy access to Winter Haven’s renowned Chain of Lakes, ideal for boating, fishing, and enjoying Florida’s outdoor lifestyle. The community also offers boat and water toy storage for a small fee, making it convenient to keep your boat or jet skis nearby and ready to use. One of the standout features of this home is the maintenance-free lifestyle. The HOA covers Cable, Internet, Exterior Home Maintenance including landscaping, mulch, and exterior painting, and More, allowing homeowners to enjoy their property without the typical upkeep responsibilities. Located just minutes from Cypress Gardens Boulevard, this home offers quick access to shopping, restaurants, grocery stores, golf courses, parks, and medical facilities. Residents are also close to LEGOLAND Florida Resort, and major roadways including US-27 and the Polk Parkway, making travel to Lakeland, Orlando, and Tampa convenient. If you’re searching for a Lake view home in Winter Haven, a low-maintenance home in a 55+ community, or a property with Ruby Lake access, 4020 Carteret Dr offers the perfect combination of location, lifestyle, and modern comfort in one of Polk County’s most established lake communities. Schedule a showing today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Sofia Lovinsky (407-376-1845)
6261 PINEHURST LOOP, WINTER HAVEN, FL 33884
$585,000103 Days on yellowkey MLS ID: L4959857
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2512 Built: 2021Monthly Fee: $5 Tax: $10,832 (2025)Community: Lake Ashton West Ph Ii NorthSpa: NoSingle Family
Taxes:$10,832
Remarks: Live the lifestyle you’ve been dreaming about in Lake Ashton, Winter Haven’s premier 55+ gated community. This beautifully cared-for Ashton floor plan offers 3 bedrooms, 2 baths, a den, and 2,512 sq ft of thoughtfully designed space — but it’s the feeling of this home that truly stands out. From the manicured landscaping to the elegant leaded-glass French front doors, every detail reflects pride of ownership. Inside, natural light pours through plantation shutters and a full wall of 8’ sliding glass doors that draw your eye straight to your private backyard retreat. The kitchen is both stylish and welcoming, featuring Seacrest Birch cabinetry with soft-close drawers, designer Silestone countertops, and elevated details that make everyday living feel special. The primary suite is a peaceful escape with custom his-and-her closets and granite makeup vanity. The flexible den space is perfect for hobbies, guests, or a home office. As a certified Green Home by Environments for Living, you’ll enjoy energy efficiency and long-term savings. Step outside and this home truly shines. The oversized screened veranda with custom flooring, a beautifully designed outdoor kitchen, and a heated saltwater pool creates the perfect setting for quiet mornings, sunset swims, or entertaining friends year-round. The extended garage offers room for longer vehicles and even a golf cart, complete with epoxy floors and screened doors. And beyond your front door? Lake Ashton delivers resort-style living with golf, fitness center, clubhouse, pickle ball, tennis, dining, and endless activities — all in a vibrant, active community. This isn’t just a home. It’s the next chapter. Washer and dryer and front flag pole do not convey.Schedule your private showing today — you’re going to love it here.
Listing Agent: Anita Lowe (863-269-6461)
3875 OSPREY POINTE CIR, WINTER HAVEN, FL 33884
$285,00020 Days on yellowkey MLS ID: O6411657
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1729 Built: 2006Monthly Fee: $210 Tax: $3,700 (2026)Community: Osprey PointeSingle Family
Taxes:$3,700
Elementary School: Garden Grove Elem
Tax Year: 2026
Remarks: This well-maintained 3-bedroom, 2-bath Garden/Patio home by Reed Builder’s Group Inc. is located in SE Winter Haven in the OSPREY POINTE community featuring maintenance-free living, a clubhouse, pool deck overlooking Lake Ned, and boat dockage availability. Situated on a premium lot, this attractive home offers 1,729 square feet of living space, a paver driveway and walkway, an attached 2-car garage, and inviting curb appeal. Built for quality and peace of mind, the home features precast concrete walls designed to withstand 140+ MPH winds, rounded corners, additional wall insulation, a tubes-in-the-wall pest defense system, security system prewire, and a leaded/beveled glass upper front door insert. Recent updates include all new windows installed approximately 5 years ago by Window World, a new roof approximately 3 years ago, and a gas hot water heater replaced approximately 2 years ago. Inside, you’ll find Mannington Jamestown oak flooring in the foyer, kitchen, and breakfast nook, with ceramic tile in the bathrooms and laundry room. The spacious living room offers vaulted ceilings, abundant natural light, and a comfortable open layout ideal for everyday living and entertaining. The kitchen features raised-panel cabinetry, granite countertops, stainless steel appliances, range is pre plumbed with gas and a bright dining area with plantation shutters. A French door out the back adds charm and convenient access to the outdoor living space. The primary suite provides a relaxing retreat with generous space, natural light, and a private bath featuring dual vanities, granite countertops, a soaking tub, and a separate glass-enclosed shower. Two additional bedrooms offer flexibility for guests, family, or a home office, and the indoor laundry room adds extra convenience also pre plumbed for gas. Washer and dryer included. Step outside and enjoy the screened lanai, paver patio, and spacious backyard, all contributing to the easy Florida lifestyle this home offers. With strong construction, thoughtful upgrades, recent big-ticket improvements, and desirable community amenities near Lake Ned, this is a standout opportunity in Winter Haven.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Jared Lippelgoos (863-224-0007)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.